Explore Kennebunkport from the water as you soak up the sun and ocean air. On this sailing trip, you'll experience Pineapple hospitality and take in local points of interest.

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$45

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Reviews

“This was our second sail on the Pineapple Ketch. The captain and mate were fantastic as always. Very informative, very lively and just an overall great atmosphere. I believe we were one of the last voyages before closing down for the season. If you have ever wanted to sail, this is a great experience. Don’t miss it.”

“Decided to take a schooner sail on a very hot day with family. It was delightful! The two man crew were friendly, professional and informative. I would recommend this to anyone who has ever had an interest in sailing in the ocean off the coast of Kennebunkport.”

“When in Maine you MUST go out onto the water. The best way to do it is on a sailing ship. The Pineapple is a two mast based in Kennebunkport Maine. This is the best way to spend a couple of relaxing hours feeling the wind and the waves (light when we were sailing) and cruise up and down the coast. High point was seeing the Bush compound but even without that tidbit, this afternoon cruise was perfect. The captain was entertaining and informative, the sea seductive. By the time we started heading back most of us were kicked back, minds empty, just soaking up the sun and sea. First time I was ever sad to return to port and the real world.”

What to Expect

  • Trips depart from the Nonantum Resort in Kennebunkport
  • Sailing trips last for two hours
  • We serve complimentary soda and water
  • Feel free to pack your favorite beverage and food

Every day is different on the water, and we sail the best route for the conditions and the day. A “normal” trip travels out of the Kennebunk River and then East along the Kennebunkport coast, past the summer cottages along Ocean Avenue and Walker’s Point, home of George and Barbara Bush. If we can make it all the way to Goat Island Lighthouse in Cape Porpoise Harbor, we have covered quite a distance before our return to Kennebunkport.

We find that the winds and seas tend to be lighter earlier in the morning and build as the day progresses, so choose a time that fits your sailing style. Complimentary soda and water are provided, but we encourage you to bring whatever snack or beverage you would like to enjoy on your trip.

Book Now
Guest
$45
Book Direct
This site is the only place to book directly with us and see live availability

Availability

Book Now
Guest
$45
Book Direct
This site is the only place to book directly with us and see live availability

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